16-bromo-2,6,10,14-tetramethyl-hexadeca-2,4,6,8,10,14-hexaene | 396090-52-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 16-bromo-2,6,10,14-tetramethyl-hexadeca-2,4,6,8,10,14-hexaene
• CAS: 396090-52-1
• 化学式: C₂₀H₂₉Br
• 分子量: 349.354
• InChiKey: NIQTYGKQMZVUKJ-XEYRODCNSA-N

物化性质

• 沸点：
  438.0±24.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  16-bromo-2,6,10,14-tetramethyl-hexadeca-2,4,6,8,10,14-hexaene 、 N-乙酰基-L-半胱氨酸甲酯 在 zinc diacetate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.0h， 以0.7 mg的产率得到2-acetylamino-3-(3,7,11,15-tetramethyl-hexadeca-2,6,8,10,12,14-hexaenylsulfanyl)-propionic acid methyl ester
  参考文献：
  名称：

  Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation

  摘要：

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.

  DOI：

  10.1021/ja0119144
• 作为产物：
  描述：

  惕格酸 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 正丁基锂 、 四溴化碳 、 硫酸 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 为溶剂， 反应 87.5h， 生成 16-bromo-2,6,10,14-tetramethyl-hexadeca-2,4,6,8,10,14-hexaene
  参考文献：
  名称：

  Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation

  摘要：

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.

  DOI：

  10.1021/ja0119144